Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines

Chem Commun (Camb). 2009 Jan 28:(4):445-7. doi: 10.1039/b813880j. Epub 2008 Nov 19.

Abstract

Using tin triflate, as an effective Lewis acid, and microwaves, direct double cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4]benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Benzodiazepines / chemical synthesis*
  • Benzodiazepinones / chemical synthesis*
  • Tin / chemistry*

Substances

  • Alkaloids
  • Benzodiazepinones
  • circumdatin F
  • sclerotigenin
  • Benzodiazepines
  • Tin
  • asperlicin C